If you are planning on taking a trip to Chicago this year, you may be feeling overwhelmed. There is so much to do and see! But don’t worry- we have some pointers that will help make your time in the Windy City an enjoyable one. Here are our top 10 tips for enjoying your Chicago vacation:
1) Pack lightly with clothes that can mix and match easily
2) Wear comfortable shoes (walking through the city can take a lot of energy!)
3) Take full advantage of public transportation; it is very easy to get around without driving or renting a car
4) Make reservations ahead of time! This ensures you’ll get into all the hot spots like restaurants, clubs, etc.
5) Make sure to have a map with you! There are tons of neighborhoods in the city, and it’s easy to get turned around
6) Make sure your pets are comfortable in a car for extended periods of time

7) Know your weather. Dress in layers!
- In the summer things will heat up quickly, so be sure to have a light dress for those hot days and a warm coat for cooler nights
- During the winter you will want some warmer clothes, but also umbrella or rain gear if it’s raining or snowing
- Also, pack some sunscreen! The sun is very strong in Chicago
- And finally, bring a good pair of sunglasses to protect your eyes from the bright city lights at night
8) Search for interesting events happening in the city during your stay- whether it’s a music festival, theatre performance or art show
- There is always something going on in Chicago!
- You can find a list of upcoming events here: [link to website]
- Another great way to find out what’s happening during your stay is to check out the local newspapers or magazines
- Some examples of Chicago publications are:Chicago Tribune, Chicago Sun-Times, and Time Out Chicago
- If you’re looking for a more specific event, try searching on websites
- And finally, don’t forget to ask the locals! They always know the best spots for food, drinks and fun
Enjoy your trip! Chicago is a beautiful city with so much to offer. These tips will help you make the most of your time here.
Terry Jones is a Chicago native who loves food and travel. He is currently a freelance photographer and also writes some articles about travel.